Senior IT Specialist

Senior IT Specialist (Weekends Required)

Shoreline Sightseeing, a Chicago landmark for over 80 years, delivers iconic river and lake experiences. Our fast-paced IT department supports a diverse range of technology across numerous locations and vessels, ensuring seamless operations for our tours and water taxi services. Join us in keeping Chicago moving!

Job Summary : We are seeking an experienced, proactive, and hands-on Senior IT Specialist to join our dynamic team. This critical role is primarily focused on providing comprehensive IT support during weekend hours, ensuring the stability, integrity, and efficient operation of IT systems across our ticketing agents, POS systems, vessels, and main office. The ideal candidate will possess advanced technical knowledge, strong troubleshooting capabilities, a collaborative mindset, and a commitment to delivering high-quality support across all levels, from direct end-user assistance to complex system resolution. Due to the nature of weekend operations, this role requires a willingness to directly address a full spectrum of IT issues as the key on-site technical resource.

Responsibilities :

• Provide comprehensive technical support (Tier 1-3) for end-users, addressing a wide range of hardware, software, and network issues via phone, email, and in-person, with a primary focus on weekend coverage. This includes both advanced troubleshooting and direct help desk assistance.
• Manage and resolve escalated issues from our IT ticketing system, ensuring detailed documentation, timely resolution, and proactive identification of recurring problems.
• Administer, maintain, and troubleshoot Windows desktops, laptops, and potentially servers, ensuring optimal performance and security.
• Ensure the reliability of POS systems and ticketing agent technology, acting as a key resource for complex transaction processing and system functionality issues.
• Assist vessel staff with technical issues related to onboard systems.
• Manage and troubleshoot network infrastructure components (switches, routers, firewalls, APs), addressing connectivity issues and ensuring network availability.
• Administer and support VPN solutions, ensuring secure and reliable remote access for users.
• Contribute to the maintenance of file servers, including permissions management, storage optimization, and ensuring data integrity.
• Manage user accounts, permissions, and group policies within Active Directory.
• Administer the Google Workspace environment, managing user accounts, security settings, and application support.
• Independently resolve a wide range of technical issues, making sound judgments on when to escalate highly complex or resource-intensive problems to specialized teams or vendors, especially those requiring weekday intervention.
• Develop and maintain technical documentation, knowledge base articles, and operational procedures.
• Proactively monitor systems, identify potential issues, and implement preventative measures.
• Collaborate effectively with other IT team members, including weekday staff for smooth handovers and knowledge sharing.
• Maintain a high level of professionalism and provide excellent customer service to all users.

Qualifications :

We'd Also Love To See :

PHYSICAL DEMANDS Intermittent physical activity including reaching, prolonged periods of sitting, bending, or lifting (up to 50lbs). Ability to climb ladders to access our vessels.

9-5 PM

3 Weekdays + 2 Weekend days, Weekends are required.